It is your responsibility to decide if you can afford it and think it worth it but most of your questions has been answered on the forum, you just have to search for it.If you can't find it here then do a some google search and call the city so you can make an educated decision.Are they zoned for 4 unit conversions into 5 units?

I also have umbrella policy through Allstate and bundle all my other coverages and it is definitely very affordable.

There's not much difference in cost going up in tiers.Buy as much insurance as you can reasonably afford if you're not wealthy enough to self-insure against reasonable possibilities. 

Also, I would analyze the properties you can afford and see what the cash flow (or other financial metrics you want to use) is after the first year or two. 

I would analyze some properties that you could afford if you did a 1031 and if you had to pay taxes on that money.  

In a roomate situation, can one cancel entire lease, even if the other one wants to stay and have lease but cant afford it without the other one paying their half? 

I was planning to self manage for a bit to keep costs down until I had enough properties to afford the PM.

For example I live in an expensive area so my main task lately is I've been researching new markets that I can afford to invest in. 

Your purchase price point may also be something you'll need to consider so you're not shopping in a great STR market, but can't afford anything in that market. 

@Kel BalaseMy parents purchased a personal residence in Katy, TX.New Houses(constructed after 2000) can be very affordable given the school districts, safety, age of home, etc.I don't invest here but I can see it working for others.